Dimethylamine → 3-(difluoro(quinolin-6-yl)methyl)-N,N-dimethylisoxazolo[4,5-b]pyridin-5-amine

HRID 219227Notes

Reaction equation

HRID 219227 reaction equation
[CH3:1][NH:2][CH3:3].Cl[C:5]1[N:10]=[C:9]2[C:11]([C:14]([F:26])([F:25])[C:15]3[CH:16]=[C:17]4[C:22](=[CH:23][CH:24]=3)[N:21]=[CH:20][CH:19]=[CH:18]4)=[N:12][O:13][C:8]2=[CH:7][CH:6]=1>C(O)C>[F:25][C:14]([F:26])([C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[N:21]=[CH:20][CH:19]=[CH:18]2)[C:11]1[C:9]2=[N:10][C:5]([N:2]([CH3:3])[CH3:1])=[CH:6][CH:7]=[C:8]2[O:13][N:12]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 576909876-((5-Chloroisoxazolo[4,5-b]pyridin-3-yl)difluoromethyl)quinoline

Product 1

HCID 576913813-(difluoro(quinolin-6-yl)methyl)-N,N-dimethylisoxazolo[4,5-b]pyridin-5-amineYield 85.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a microwave vial was added dimethylamine (2.0 M in THF, 0.75 mL, 1.5 mmol) and, 6-((5-chloroisoxazolo[4,5-b]pyridin-3-yl)difluoromethyl)quinoline (0.10 g, 0.30 mmol) in ethanol (3 mL). The mixture was stirred at 140° under microwave irradiation for two hours then was concentrated and purified by MPLC (eluted with a gradient of 10 to 50% ethyl acetate in hexanes) to yield the product as a light yellow solid (87 mg, 85%). MS m/z=341.2 [M+1]+ Calc'd for C18H14F2N4O: 340.3.

Workup

  1. concentrationthen was concentrated
  2. custompurified by MPLC (
  3. washeluted with a gradient of 10 to 50% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-ff1fcba0daa04825b6fe98a496450c06
Source dataset
uspto-grants-2012_06
Patent number
US08198448B2

Reaction notes

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